Benzyl Bromide → (S)-ethyl 2-(2-(1-benzyl-3-methyl-1H-indazol-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879562Notes

Reaction equation

HRID 879562 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:30]([CH3:31])=[CH:29][C:15]2[N:16]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][N:23]=[C:22]4[CH3:28])[S:18][C:14]=2[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:45](Br)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(#N)C>[CH2:45]([N:24]1[C:25]2[C:21](=[CH:20][C:19]([C:17]3[S:18][C:14]4[C:13]([C:32]5[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=5)=[C:12]([C@H:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:30]([CH3:31])=[CH:29][C:15]=4[N:16]=3)=[CH:27][CH:26]=2)[C:22]([CH3:28])=[N:23]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178472573HCID 178472573, compound

Product 1

HCID 86700386(S)-ethyl 2-(2-(1-benzyl-3-methyl-1H-indazol-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a stirring solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate (219 mg, 0.4 mmol) in ACN (5 mL) was added K2CO3 (166 mg, 1.2 mmol) and benzyl bromide (71 μL, 0.6 mmol). The reaction was then heated to 75° C. for 27 hours. After cooling to room temperature, the solids were filtered off, the crude reaction was concentrated and purified by column chromatography (gradient 0 to 20% EtOAc in hexanes) to give (S)-ethyl 2-(2-(1-benzyl-3-methyl-1H-indazol-5-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 8.05 (d, J=8.9 Hz, 1H), 7.92 (s, 1H), 7.60-7.45 (m, 4H), 7.35-7.27 (m, 4H), 7.22-7.18 (m, 2H), 5.54 (s, 2H), 5.16 (s, 1H), 4.21 (dtt, J=10.9, 7.4, 3.7 Hz, 2H), 2.63 (s, 3H), 2.60 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 0.98 (s, 9H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solids were filtered off
  3. customthe crude reaction
  4. concentrationwas concentrated
  5. custompurified by column chromatography (gradient 0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d667417e10b943f296a0da67148a8f55
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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