2-Chlorobenzimidazole → n-(Benzimidazol-2-yl)-5-bromo-1-indanylamine

HRID 16549Notes

Reaction equation

Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][CH:12]1[C:20]2[C:15](=[CH:16][C:17]([Br:21])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>>[N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[NH:3][C:2]=1[NH:11][CH:12]1[C:20]2[C:15](=[CH:16][C:17]([Br:21])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

Reactant 2

HCID 785722-Chlorobenzimidazole

HCID 222283885-bromo-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 11624041n-(Benzimidazol-2-yl)-5-bromo-1-indanylamine

Procedure

The title compound was prepared from 2-chlorobenzimidazole and racemic 1-amino-5-bromoindane (prepared by Procedure B from 5-bromo-1-indanone) by Procedure A (30 min at 170° C.). The product was isolated by preparative LCMS to give the title compound as the free base and as a mixture of enantiomers (white solid, mp 242-243° C.). MS(ES+) m/z 328 ([M+1]+, 100). 1NMR (DMSO-d6) δ 1.92 (m, 1H), 2.50 (m, 1H), 2.83 (m, 1H), 2.95 (m, 1H), 5.35 (m, 1H), 6.82-7.02 (m, 3H), 7.12-7.35 (m, 4H), 7.46 (s, 1H), 10.7 (s, 1H).

Workup

customThe product was isolated by preparative LCMS

Sources & evidence

ORD record: ord-1af200ca71724ded997ce2ce2a9d94a6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737167B2

Reaction notes

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