Potassium Carbonate → (S)-3-((1-(4-chlorophenyl)piperidin-4-yl)methyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

HRID 1645020Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11](=[CH2:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.B1C2CCCC1CCC2.Br[C:25]1[CH:34]=[N:33][C:32]2[N:31]3[CH2:35][CH2:36][CH2:37][C@H:30]3[C:29](=[O:38])[NH:28][C:27]=2[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][C:25]3[CH:34]=[N:33][C:32]4[N:31]5[CH2:35][CH2:36][CH2:37][C@H:30]5[C:29](=[O:38])[NH:28][C:27]=4[CH:26]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

1-(4-chlorophenyl)-4-methylenepiperidine (70 mg, 0.337 mmol) was diluted with 0.5M THF solution of 9-BBN (0.674 mL, 0.337 mmol) under nitrogen and stirred at 75° C. for 1 h. The reaction mixture was then added to a suspension of (S)-3-bromo-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (90 mg, 0.337 mmol), PdCl2(dppf)-CH2Cl2 adduct (8.26 mg, 10.11 μmol) and potassium carbonate (93 mg, 0.674 mmol) in DMF (1.0 mL) and water (0.1 mL) and stirred at 60° C. for 4 h.

Workup

stirringstirred at 60° C. for 4 h.

Sources & evidence

ORD record: ord-06303f3a995448359328575433baba51
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124606B2

Reaction notes

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