1,2,3,4-Tetrahydroquinoline → HCID 67332018, compound

HRID 1669648Notes

Reaction equation

[F:1][C:2]([F:34])([F:33])[CH:3]1[CH2:8][CH2:7][C:6]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)([C:9]2[CH:14]=[CH:13][C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[NH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:35]1([C:12]2[CH:13]=[CH:14][C:9]([C:6]3([C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=4)[CH2:7][CH2:8][CH:3]([C:2]([F:34])([F:1])[F:33])[CH2:4][CH2:5]3)=[CH:10][CH:11]=2)[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of the title compound of Example 3, Step A (50 mg, 0.1 mmol), 1,2,3,4-tetrahydroquinoline (0.019 mL, 0.15 mmol), 2-(di-tert-butylphosphino)biphenyl (1 mg, 0.003 mmol), palladium (II) acetate (0.5 mg, 0.002 mmol) and sodium tert-butoxide (13 mg, 0.14 mmol) was added 0.30 mL of toluene. The reaction was stirred at 90° C. for 16 h, then partitioned between EtOAc/brine acidified with a few drops of 2 N HCl. The aqueous layer was washed with EtOAc then DCM. The combined organic layers were concentrated under reduced pressure to provide the product as a mixture of the title methyl ester and the hydrolyzed carboxylic acid. LC-MS (ESI): m/z=494.3 [M+1]+.

Workup

custompartitioned between EtOAc/brine
washThe aqueous layer was washed with EtOAc
concentrationThe combined organic layers were concentrated under reduced pressure
customto provide the product

Sources & evidence

ORD record: ord-9c93945006624ab98c0e36551ef94b6c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989472B2

Reaction notes

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