(3-Chlorophenyl)boronic acid → HCID 59807916, compound

HRID 912574Notes

Reaction equation

HRID 912574 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:18]=[C:17]([CH3:19])[N:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3Br)[C:15]=2[CH3:27])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1>COCCOC.CCO.C([O-])([O-])=O.[Na+].[Na+].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]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:18]=[C:17]([CH3:19])[N:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:28])[CH:34]=3)[C:15]=2[CH3:27])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 59807653HCID 59807653, compound

Product 1

HCID 59807916HCID 59807916, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10340Sodium CarbonateSolventHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 1-(2-bromophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl)-amide (100 mg, 0.23 mmol) and 3-chlorophenylboronic acid (0.95 g, 0.57 mmol) in DME/EtOH (2:1, 5 mL), 1M Na2CO3 (0.80 mL) and Pd(dppf)2Cl2 (38 mg, 0.046 mmol) were added. The reaction mixture was degassed and heated at 80° C. under Argon for 1 h and monitored by LC-MS. The mixture was diluted with DCM (20 mL) and washed with 15 mL of brine. The aqueous phase was extracted with DCM (20 mL) twice. The combined extracts were dried over anhyd Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel, eluting with EtOAc-Hex (0-50%) to yield the title compound (53 mg, 48%) as a pale yellow solid. 1H-NMR (CDCl3): δ 7.89 (2H, d), 7.80 (2H, d), 7.65 (1H, s), 7.57 (3H, m), 7.26 (3H, m), 7.04 (1H, t), 6.87 (1H, m), 6.13 (1H, s), 3.03 (3H, s), 2.23 (3H, s), 1.89 (3H, s). MS (ESI): 479 (MH+).

Workup

  1. customThe reaction mixture was degassed
  2. additionThe mixture was diluted with DCM (20 mL)
  3. washwashed with 15 mL of brine
  4. extractionThe aqueous phase was extracted with DCM (20 mL) twice
  5. dry with materialThe combined extracts were dried over anhyd Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by flash chromatography on silica gel
  8. washeluting with EtOAc-Hex (0-50%)

Sources & evidence

ORD record
ord-d03421bf465741ca87c92357e68b9c68
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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