Potassium Phosphate, Tribasic → HCID 59455010, compound

HRID 1401624Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[CH:6]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:29][N:30]1[CH2:43][CH2:42][C:33]2[NH:34][C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]=2[CH2:31]1>CN(C=O)C.[Cu]I>[Cl:12][C:7]1[CH:6]=[C:5](/[C:3](/[CH3:4])=[CH:2]/[N:34]2[C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]3[CH2:31][N:30]([CH3:29])[CH2:43][CH2:42][C:33]2=3)[CH:10]=[C:9]([Cl:11])[CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

1-(2-Bromo-1-methyl-vinyl)-3,5-dichloro-benzene (315 mg, 1.2 mmol) was dissolved in DMF (2 mL) and potassium phosphate (414 mg, 2 mmol) was added followed by CuI (19 mg, 0.1 mmol), L-Proline (23 mg, 0.2 mmol) and 2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.2 g, 1 mmol). Nitrogen was purged in the reaction mixture for 5 min and the contents stirred at 85° C. overnight. The reaction mixture was poured into ice water (10 mL) to get the solid mass which was filtered off under vacuum. The residue obtained was purified through reverse phase HPLC to get desired product. 1H NMR (CD3OD, oxalate salt) δ (ppm): 7.80 (s, 1H), 7.50 (s, 2H), 7.38 (s, 1H), 7.20 (s, 1H), 7.0 (m, 2H), 4.42 (m, 2H), 3.60 (m, 2H), 3.05 (m, 2H), 3.0 (s, 3H), 2.38 (s, 3H), 1.82 (s, 3H).

Workup

customNitrogen was purged in the reaction mixture for 5 min
additionThe reaction mixture was poured into ice water (10 mL)
customto get the solid mass which
filtrationwas filtered off under vacuum
customThe residue obtained
customwas purified through reverse phase HPLC

Sources & evidence

ORD record: ord-ba9e1a3762244242bc7301db08f0605b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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