Potassium Carbonate → HCID 68856363, compound

HRID 1453892Notes

Reaction equation

HRID 1453892 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C@@H:11]([CH3:25])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[C:20]=2[CH:22]=O)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH2:38]([O:37][C:35]([C:34]1[O:24][C:19]2=[CH:18][CH:17]=[C:16]3[C:21]([N:13]([CH2:12][C@@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:26])[CH3:25])[N:14]=[CH:15]3)=[C:20]2[CH:22]=1)=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 62576Benzyl bromoacetateHCID 136385114Benzyl [(1S)-2-(7-formyl-6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate

Product 1

HCID 68856363HCID 68856363, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of the product from Step C, Example 1 (0.12 g, 0.32 mmol) in DMF (10 mL) was added potassium carbonate (0.15 g, 1.05 mmol) followed by benzyl 2-bromoacetate (0.08 g, 0.48 mmol) at room temperature and the mixture was heated at 70° C. for 20 h. A saturated aqueous solution of ammonium chloride (20 mL) was added followed by ethyl acetate (50 mL). The organic layer was separated and the aqueous was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated to a residue, which was purified by chromatography (silica, 50% ethyl acetate in hexane) to give a solid (0.11 g, 71%): mp 140-141° C.; MS (ES) m/z 484 (M+).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. customdried
  5. customevaporated to a residue, which
  6. customwas purified by chromatography (silica, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bf1daf8d1fac4e24b0f33a502006a7a1
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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