Cesium carbonate → HCID 86650844, compound

HRID 1028223Notes

Reaction equation

HRID 1028223 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5]2.Cl[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:15]([O:14][C:12]([N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:20]3[S:21][C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH:3]=2)[CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 119872-ChlorobenzothiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 86650844HCID 86650844, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A toluene solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (248 mg), 2-chlorobenzothiazole (186 mg), palladium acetate (22 mg), cesium carbonate (651 mg), and Xantphos (58 mg) was stirred at 120° C. for 1 hour under microwave irradiation. The reaction solution was purified by column chromatography to obtain the title compound (381 mg, quantitative yield).

Workup

  1. customThe reaction solution was purified by column chromatography

Sources & evidence

ORD record
ord-02fc729b42e647c3b557f98b9b5c071f
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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