tert-Butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate → 5-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 2183719Notes

Reaction equation

[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[Sn](CCCC)(CCCC)CCCC)([CH3:4])([CH3:3])[CH3:2].[C:28]([O:32][C:33]([N:35]1[CH2:44][CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2Br)[CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C1(PC2C=CC=CC=2C2C=CC=CC=2)CCCCC1>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.[Pd]>[C:28]([O:32][C:33]([N:35]1[CH2:44][CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:27])[CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3-tributylstannyl-pyridin-4-yl)-carbamic acid tert-butyl ester (0.7 g, 1.44 mmol), 5-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.45 g, 1.44 mmol), tris(dibenzylideneacetone)dipalladium(O) (0.066 g, 0.072 mmol) and 2-(cyclohexylphosphino)biphenyl (0.075 g, 0.216 mmol), in toluene was heated with stirring to 100° C. for 24 h. The solvent was evaporated and the residue purified by flash chromatography eluting with 50% ethyl acetate in hexanes to yield 0.18 g 5-(4-tert-butoxycarbonylamino-pyridin-3-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester).

Workup

customThe solvent was evaporated
customthe residue purified by flash chromatography
washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-1931d85e807a4f678ff1b8f56c61755f
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900220B2

Reaction notes

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