(R)-(-)-1-Aminoindan → HCID 44217313, compound

HRID 1931474Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:8]=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:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[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)[CH:11]=[CH:10]3)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 2733933(R)-(-)-1-Aminoindan

HCID 85854015HCID 85854015, compound

Product 1

HCID 44217313HCID 44217313, compoundYield 8%

Conditions

Temperature: 130 °C

Procedure

A stirred mixture of 2-chloro-6-(4-fluoro-benzyloxy)-quinoline (0.08 g, 0.4 mmol) and (R)-1-aminoindane (0.107 g, 1.00 mmol) was heated in a sealed tube for 20 h at 130° C. Purification by flash chromatography on silica gel (ethyl acetate in heptane, 0→80%) yielded the title compound as a dark oil (9 mg, 8%), MS 385.6 [(M+H)+].

Workup

customPurification by flash chromatography on silica gel (ethyl acetate in heptane, 0→80%)

Sources & evidence

ORD record: ord-dcd1f385feac4e2d9b2659417a084765
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188284B2

Reaction notes

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