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 8963Notes

Reaction equation

HRID 8963 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-ff392881b94248d4b1fd278693bd58ef
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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