Water → HCID 59494206, compound

HRID 872035Notes

Reaction equation

HRID 872035 reaction equation
B1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)C2CCCC1CCC2.Br[C:18]1[C:26]2[C:21](=[CH:22][C:23]([CH2:27][N:28]([CH:36]3[CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:24][CH:25]=2)[N:20]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[N:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCCC1.CN(C)C=O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH2:10]([C:18]1[C:26]2[C:21](=[CH:22][C:23]([CH2:27][N:28]([CH:36]3[CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:24][CH:25]=2)[N:20]([CH2:39][CH2:40][CH2:41][O:42][CH3:43])[N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 59494314HCID 59494314, compound

Product 1

HCID 59494206HCID 59494206, compound

Reagents, catalysts & solvents 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 0.5M solution of B-benzyl-9-BBN in tetrahydrofuran (1.8 ml) was added to a solution of tert-butyl {[3-bromo-1-(3-methoxypropyl)-1H-indazol-6-yl]methy}cyclopropylcarbamate (200 mg), potassium phosphate (290 mg), palladium acetate(II) (4 mg) and S-Phos (15 mg) in N,N-dimethylformamide (5 ml) under argon atmosphere and the mixture was stirred at 60° C. for 18 hours. Water was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane to n-hexane/ethyl acetate=2/1) to give tert-butyl {[3-benzyl-1-(3-methoxypropyl)-1H-indazol-6-yl]methy}cyclopropylcarbamate (198 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane to n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-37b67b84638d48f9a01ecfd7cbc791cf
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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