Sodium Carbonate → tert-Butyl 6-(pyridin-4-yl)indoline-1-carboxylate

HRID 1628291Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[N:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][N:8]3[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 20 ml vial was added tert-butyl 6-bromoindoline-1-carboxylate 50.A (500 mg, 1.7 mmole), 4-pyridylboronic acid (309 mg, 2.5 mmol), tetrakis(triphenylphosphine) palladium(388, 0.34 mmol), DMF and 3 ml of saturated sodium carbonate. The reaction was stirred at 70° C. for 6 hours at which time the reaction mixture was partitioned between 300 ml EtAc and 200 ml of water. The organic solvent was removed by rotary evaporation and the crude product purified by reverse phase preparative HPLC to give tert-butyl 6-(pyridin-4-yl)indoline-1-carboxylate 50.B as a yellow solid (202 mg, 41% yield).

Workup

customwas partitioned between 300 ml EtAc and 200 ml of water
customThe organic solvent was removed by rotary evaporation
customthe crude product purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-42a8990ab842480da2e9a5031f646b37
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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