HCID 58298516, compound → HCID 58298438, compound

HRID 603118Notes

Reaction equation

HRID 603118 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-9f3bcb06774a48218e6167bca8cce2bd
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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