Chloroacetaldehyde → HCID 59129491, compound

HRID 468477Notes

Reaction equation

HRID 468477 reaction equation
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:19][CH2:18]3)=[O:16])[CH:11]=2)[N:6]1[CH2:31][CH2:32]C#N)([CH3:4])([CH3:3])[CH3:2].[Cl:35]CC=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:15]([C:17]3([C:20]4[CH:30]=[CH:29][C:23]5[O:24][C:25]([F:28])([F:27])[O:26][C:22]=5[CH:21]=4)[CH2:19][CH2:18]3)=[O:16])[CH:11]=2)[N:6]1[CH2:31][CH2:32][Cl:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59129217HCID 59129217, compound

Product 1

HCID 59129491HCID 59129491, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-tert-butyl-1-(2-cyanoethyl)indolin-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (71 mg, 0.17 mmol) in anhydrous dichloromethane (1 mL) was added chloroacetaldehyde (53 μL, 0.41 mmol) at room temperature under N2. After 20 mm of stirring, NaBH(OAc)3 (90 mg, 0.42 mmol) was added in two portions. The reaction mixture was stirred overnight at room temperature. The product was purified by column chromatography on silica gel (2-15% ethyl acetate/hexanes) providing N-(2-tert-butyl-1-(2-chloroethyl)indolin-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (51 mg, 63%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customThe product was purified by column chromatography on silica gel (2-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-be899f163bd84d6e89f081d3a21a0ae1
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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