HCID 58298516, compound → HCID 58298438, compound

HRID 419951Notes

Reaction equation

HRID 419951 reaction equation
C([O:3][CH2:4][CH2:5][N:6]1[C:10]2[C:11]([F:16])=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1)=O>CO.C(N(CC)CC)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[N:8]=[CH:7][N:6]([CH2:5][CH2:4][OH:3])[C:10]=2[C:11]=1[F:16]

Participants

4

Reactant 1

HCID 58298516HCID 58298516, compound

Product 1

HCID 58298438HCID 58298438, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

2-(6-Chloro-7-fluoro-1H-benzimidazol-1-yl)ethyl formate (1.1 g, 4.53 mmol) is dissolved in MeOH (50.0 mL) with triethylamine (5.0 mL) and stirred at room temperature 18 hours. The reaction mixture is then concentrated to provide the expected product 2-(6-chloro-7-fluoro-1H-benzimidazol-1-yl)ethanol (0.95 g, 98%) as a white powder. 1H NMR (400 MHz, METHANOL-D4) δ ppm 3.90 (t, J=4.69 Hz, 2H) 4.47 (t, J=5.08 Hz, 2H) 7.30 (dd, J=8.79, 6.84 Hz, 1H) 7.45 (dd, J=8.59, 0.78 Hz, 1H) 8.16-8.19 (m, 1H)

Workup

  1. concentrationThe reaction mixture is then concentrated

Sources & evidence

ORD record
ord-216e231f01fb48279fc94fe1759a9275
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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