Potassium Phosphate, Tribasic → HCID 86663034, compound

HRID 2410781Notes

Reaction equation

HRID 2410781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[C:14]([C:27]([O:29][CH3:30])=[O:28])[C:15]2[NH:16][C:17]3[CH:18]=[C:19]([CH:25]=[O:26])[CH:20]=[CH:21][C:22]=3[C:23]=2[N:24]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([C:27]([O:29][CH3:30])=[O:28])[C:15]3[NH:16][C:17]4[CH:18]=[C:19]([CH:25]=[O:26])[CH:20]=[CH:21][C:22]=4[C:23]=3[N:24]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734323(3-Chlorophenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86663035HCID 86663035, compound

Product 1

HCID 86663034HCID 86663034, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of 3-chlorophenylboronic acid (73.8 mg, 0.472 mmol), methyl 2-bromo-7-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (131 mg, 0.393 mmol), powdered potassium phosphate tribasic (200 mg, 0.944 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (32.3 mg, 0.079 mmol), and Pd(OAc)2 (8.8 mg, 0.039 mmol) in a microwave vial was flushed with nitrogen. THF (2 mL) was added, the vial was capped and the reaction was heated in a 70° C. oil bath for 24 hr. The reaction was partitioned between EtOAc (10 mL) and water (10 mL). The precipitate was collected by filtration, washed with EtOAc and water and air dried to leave methyl 2-(3-chlorophenyl)-7-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (88 mg, 0.24 mmol, 61% yield) as a yellow solid. MS (ESI) m/z 364.99 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04 (1H, br. s.), 10.18 (1H, s), 8.47 (1H, d, J=8.06 Hz), 8.41 (1H, s), 8.28 (1H, s), 8.25 (1H, s), 8.17 (1 H, d, J=7.55 Hz), 7.83 (1H, d, J=8.06 Hz), 7.56 (1H, t, J=7.81 Hz), 7.47-7.53 (1H, m), 4.07 (3H, s).

Workup

  1. customwas flushed with nitrogen
  2. additionTHF (2 mL) was added
  3. customthe vial was capped
  4. customThe reaction was partitioned between EtOAc (10 mL) and water (10 mL)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with EtOAc and water and air
  7. customdried

Sources & evidence

ORD record
ord-e0be5165fa64485fbd598b5472335c29
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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