Sodium Carbonate → HCID 57801560, compound

HRID 1669856Notes

Reaction equation

HRID 1669856 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:19])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=3)[CH:9]=2)=[CH:4][CH:3]=1.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:2]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([NH:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:19])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 10008274HCID 10008274, compound

Product 1

HCID 57801560HCID 57801560, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from example 79 step F (50 mg, 0.079 mmol) in toluene (1 mL) was added phenyl boronic acid (10 mg, 0.079 mmol), Na2CO3 solution (2.0M, 79 uL) and tetrakis triphenyl phosphine palladium (0) (5 mg, 0.003 mmol). The resulting mixture was placed in the CEM microwave instrument for 10 min at a temperature of 100° C. and power 150 W. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 3:10 ethyl acetate-hexanes to give the desired product, a colorless oil. To a solution of this material in DCM (2 mL) was added trifluoroacetic acid (2 mL). The reaction was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and lyophilized from acetonitrile-water to give the title compound. 1H NMR (DMSO, 500 MHz): δ 8.5 (t, J=5.5 Hz, 1H), 7.91 (d, J=1.9 Hz, 2H), 7.81 (d, J=8.2 Hz, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.74 (d, J=7.3 Hz, 2H), 7.58 (m, 3H), 7.51 (t, J=7.6 Hz, 2H), 7.42 (t, J=7.6 Hz, 1H), 7.25 (s, 1H), 7.15 (d, J=8.2 Hz, 2H), 5.56 (s, 2H), 3.45 (q, J=7.1 Hz, 2H), 2.47 (t, J=7.1 Hz, 2H). LC-MS: 2.73 min; (M+H)=570.1.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0a121447cd7340aaaf729c8164522246
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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