Acetyl chloride → HCID 86592028, compound

HRID 1349545Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C@H:14]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:13][C@@H:12]2[CH3:28])=[O:10])[CH:6]=[CH:7][CH:8]=1.[C:29](Cl)(=[O:31])[CH3:30]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[C:29](=[O:31])[CH3:30])[CH2:13][C@@H:12]1[CH3:28])=[O:10]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 86592029HCID 86592029, compound

Product 1

HCID 86592028HCID 86592028, compound

Procedure

Pd2(dba)3 (0.05 equ.), and rac-BINAP (0.1 equ.) were added to a flask with degassed toluene and stirred for 1 h. To the above solution was added 2-bromopyridine (1.1 equ.) and NaOtBu (1.1 equ.) and stirred for 30 min. (±)-Cis-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(3-methoxy-phenyl)-methanone was dissolved in degassed toluene and added to the solution and heated to 100° C. for 17 h. The reaction was diluted with ether and filtered through celite and concentrated down. The compound was purified by Biotage with 20% EtOAc/80% Hexane to 30% EtOAc/70% Hexane to 50% EtOAc/50% Hexane to give 43% of the product. (±)-Cis-(3-methoxy-phenyl)-[2-methyl-4-(pyridin-2-ylamino)-3,4-dihydro-2H-quinolin-1-yl]-methanone was acetylated with acetyl chloride as previously described to give (±)-cis-N-[1-(3-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-pyridin-2-yl-acetamide.

Sources & evidence

ORD record: ord-e3149ce091da4d29b98e35bf5c2499d3
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211672B2

Reaction notes

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