(R)-(-)-1-Aminoindan → [5-(4-Fluoro-benzyloxy)-quinolin-2-yl]-(R)-indan-1-yl-amine

HRID 2076279Notes

Reaction equation

HRID 2076279 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[N:3]=1.[NH2:21][C@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][O:12][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[CH:10]=[CH:11][C:2]([NH:21][C@H:22]2[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:24][CH2:23]2)=[N:3]3)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 2733933(R)-(-)-1-AminoindanHCID 866194962-Chloro-5-(4-fluoro-benzyloxy)-quinoline

Product 1

HCID 67095974[5-(4-Fluoro-benzyloxy)-quinolin-2-yl]-(R)-indan-1-yl-amine

Procedure

2-Chloro-5-(4-fluoro-benzyloxy)-quinoline (100 mg, 0.347 mmol) and (R)-1-aminoindane (138 mg, 1.04 mmol) were stirred in a sealed tube at 150° C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 75:25). The title compound was obtained as a light brown oil (68 mg, 51%), MS: m/e=385 (M+H+).

Workup

  1. customThe reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 75:25)

Sources & evidence

ORD record
ord-4f11c968eed24962ab403eacf1b0d1c4
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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