Cyclopropanecarboxaldehyde → HCID 59835866, compound

HRID 271726Notes

Reaction equation

HRID 271726 reaction equation
[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH2:30][CH2:31][NH:32][CH2:33][CH:34]3[CH2:36][CH2:35]3)[CH:25]=[CH:24]4)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO.C(O)(=O)C>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH2:30][CH2:31][N:32]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH2:33][CH:34]3[CH2:35][CH2:36]3)[CH:25]=[CH:24]4)=[N:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 4311764Sodium borohydrideHCID 59835834(2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-cyclopropylmethyl-amine

Product 1

HCID 59835866HCID 59835866, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

36 μL (0.47 mmol) cyclopropanecarbaldehyde are added to a solution of 100 mg (0.24 mmol) (2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-cyclopropylmethyl-amine in 20 mL MeOH at RT and 15 min later 59 mg (0.94 mmol) NaBH4 and one drop of glacial acetic acid are added. The mixture is stirred for 1 h at RT, evaporated down i.vac., the residue is taken up in dilute K2CO3 solution, extracted exhaustively with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is triturated with PE, suction filtered and dried.

Workup

  1. additionare added
  2. customevaporated down i.vac
  3. extractionextracted exhaustively with EtOAc
  4. dry with materialdried over Na2SO4
  5. customis triturated with PE, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-06822aefe0ec4745b3fac509b8a95db3
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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