Methyl 4-hydroxy-1,2-dimethyl-1H-benzo[d]imidazole-6-carboxylate → Methyl 4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazole-6-carboxylate

HRID 2238594Notes

Reaction equation

HRID 2238594 reaction equation
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=2[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=1.Cl[CH:18]1[C:27]2[C:22](=[CH:23][C:24]([F:29])=[CH:25][C:26]=2[F:28])[O:21][CH2:20][CH2:19]1>>[F:28][C:26]1[CH:25]=[C:24]([F:29])[CH:23]=[C:22]2[C:27]=1[CH:18]([O:1][C:2]1[C:10]3[N:9]=[C:8]([CH3:11])[N:7]([CH3:12])[C:6]=3[CH:5]=[C:4]([C:13]([O:15][CH3:16])=[O:14])[CH:3]=1)[CH2:19][CH2:20][O:21]2

Participants

3

Reactant 2

HCID 68690597Methyl 4-hydroxy-1,2-dimethyl-1H-benzo[d]imidazole-6-carboxylateHCID 686921254-Chloro-5,7-difluorochromane

Product 1

HCID 68688755Methyl 4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-1,2-dimethyl-1H-benzimidazole-6-carboxylateYield 59%

Procedure

The title compound was prepared as a white solid in 59% yield (3.2 g) from methyl 4-hydroxy-1,2-dimethyl-1H-benzimidazole-6-carboxylate (3.0 g, 14 mmol, WO 2004054984) and 4-chloro-5,7-difluorochromane (4.7 g, 21 mmol, STEP 2 of Example 5) by the same manner in STEP 1 of Example 11.

Sources & evidence

ORD record
ord-47ded00829954c05b0379f0a040129b9
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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