2,3-Dihydro-1-benzofuran-3-amine → HCID 67095778, compound

HRID 2076287Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:12][S:13]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)(=[O:15])=[O:14])[N:3]=1.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]([NH2:34])[CH2:26]1>O1CCOCC1>[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]([NH:34][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][C:8]=3[NH:12][S:13]([C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=3)(=[O:15])=[O:14])[N:3]=2)[CH2:26]1

Participants

Conditions

Temperature: 120 °C

Procedure

N-(2-Chloro-quinolin-5-yl)-3,4,5-trifluoro-benzenesulfonamide (150 mg, 0.402 mmol) was dissolved in 5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. rac-2,3-Dihydro-benzofuran-3-ylamine (CAS 109926-35-4, 82 mg, 0.607 mmol), sodium tert.-butylate (97 mg, 1.01 mmol), 1,1′-bis(diphenylphosphin)ferrocen (33 mg, 0.06 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II) chloride (16 mg, 0.02 mmol) were added. The reaction mixture was stirred in a sealed tube at 120° C. for 6 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->70:30 gradient). The title compound was obtained as a yellow foam (100 mg, 53%), MS: m/e 472.4 (M+H+).

Workup

customArgon was bubbled through the solution for 2 minutes
customto remove oxygen
customThe solvent was evaporated
customthe residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->70:30 gradient)

Sources & evidence

ORD record: ord-a4c9fb7ba0734ab89ffbc4a1099fb7a1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923561B2

Reaction notes

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