2,3-Dihydro-1-benzofuran-7-carbaldehyde → (1H-Benzimidazol-2-ylmethyl)-(2,3-dihydro-benzofuran-7-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 1582300Notes

Reaction equation

HRID 1582300 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(OC([N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28][NH:29][CH:30]1[C:39]2[N:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH2:33][CH2:32][CH2:31]1)=O)(C)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[NH:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28][N:29]([CH2:10][C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)[CH:30]1[C:39]2[N:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 219850812-[(5,6,7,8-Tetrahydroquinolin-8-ylamino)-methyl]-benzimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 21984995(1H-Benzimidazol-2-ylmethyl)-(2,3-dihydro-benzofuran-7-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Procedure

Following General Procedure B: To a solution of 2,3-dihydrobenzofuran-7-carboxaldehyde (53.6 mg, 0.362 mmol) and [1-(tert-butoxycarbonyl)-(1H-benzimidazol-2-ylmethyl)]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (136 mg, 0.361 mmol) CH2Cl2 (5 mL) was added NaBH(OAc)3 (112 mg, 0.528 mmol) and the mixture stirred overnight. Purification of the crude product by radial chromatography on silica gel (1 mm TLC plate, 125:1:1 CH2Cl2: CH3OH: NH4OH) to gave the desired freebase (48 mg, 33%).

Workup

  1. customPurification of the crude product by radial chromatography on silica gel (1 mm TLC plate, 125:1:1 CH2Cl2: CH3OH: NH4OH)
  2. customto gave the desired freebase (48 mg, 33%)

Sources & evidence

ORD record
ord-5e979fe7e8e1467c9b1e9ca7c246366e
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Reaction notes

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