Acetate → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3,4-dimethoxyphenyl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

HRID 879400Notes

Reaction equation

HRID 879400 reaction equation
C([O-])(=O)C.[C:5]([O:9][C@@H:10]([C:16]1[C:31]([CH3:32])=[CH:30][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=3)[S:22][C:18]=2[C:17]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:11]([O:13]CC)=[O:12])([CH3:8])([CH3:7])[CH3:6].[CH3:40][O:41][C:42]1[CH:43]=[C:44](B(O)O)[CH:45]=[CH:46][C:47]=1[O:48][CH3:49].C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([O:9][C@@H:10]([C:16]1[C:31]([CH3:32])=[CH:30][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:45]4[CH:44]=[CH:43][C:42]([O:41][CH3:40])=[C:47]([O:48][CH3:49])[CH:46]=4)[N:24]=3)[S:22][C:18]=2[C:17]=1[C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1)[C:11]([OH:13])=[O:12])([CH3:7])([CH3:6])[CH3:8]

Participants

6

Reactant 4

HCID 175AcetateHCID 11430Potassium CarbonateHCID 27347023,4-Dimethoxyphenylboronic acidHCID 86700205(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 72195975(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(3,4-dimethoxyphenyl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

Preparation of (S)-ethyl 2-tert-butoxy-247-(4-chlorophenyl)-2-(2-(3,4-dimethoxyphenyl)pyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate: (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (50.0 mg, 0.094 mmol), 3,4-dimethoxyphenylboronic acid (20.6 mg, 0.113 mmol), tetrakis(triphenylphosphine)palladium(0) (16.4 mg, 0.014 mmol), and K2CO3 (39.2 mg, 0.283 mmol) were taken in a microwave vial, and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed 1,4-dioxane (1 mL) and degassed water (0.25 mL). The reaction mixture was stirred at 110° C. for 1.5 h, filtered through Celite (ethyl acetate eluent), and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. LCMS-ESI+ calc'd for C34H35ClN3O5S (M+H+): 632.2; Found: 632.2 (M+H+).

Workup

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed 1,4-dioxane (1 mL)
  4. customdegassed water (0.25 mL)
  5. filtrationfiltered through Celite (ethyl acetate eluent)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  8. customprovided the product

Sources & evidence

ORD record
ord-abd6b69df7e043929d8b9ff59468a9f2
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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