Indoline → HCID 58547567, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19](Br)=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
7
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-bromo-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (94) (280 mg, 0.82 mmol), 2,3-dihydro-1H-indole (97 mg, 0.82 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), BINAP (24 mg, 0.04 mmol) and t-BuONa (173 mg, 1.64 mmol) in toluene (20 mL) was stirred at 100° C. for 12 h. The mixture was left to reach RT and filtered through a pad of Celite and the filter cake was washed with CH2Cl2 (30 mL). The combine filtrate was evaporated in vacuo and the residue was purified by flash column chromatography (20% to 40% EtOAc in petroleum ether) to afford 3-(2,3-dihydro-indol-1-yl)-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (95) (100 mg, 0.29 mmol, yield 32%).
Workup
- waitThe mixture was left
- customto reach RT
- filtrationfiltered through a pad of Celite
- washthe filter cake was washed with CH2Cl2 (30 mL)
- customThe combine filtrate was evaporated in vacuo
- customthe residue was purified by flash column chromatography (20% to 40% EtOAc in petroleum ether)
Sources & evidence
- ORD record
- ord-1b85f7aa35214c04b4a5cc416325a9f3
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957073B2
Reaction notes
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