Dichloromethane → HCID 73443602, compound

HRID 991560Notes

Reaction equation

HRID 991560 reaction equation
Br[C:2]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:34])[C:26]2[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=2[Cl:33])=[CH:20][CH:19]=1)=[C:3]([NH:8][C:9]([C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10])[C:4]([O:6][CH3:7])=[O:5].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:12]1[C:11]([C:9]([NH:8][C:3](=[C:2]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:34])[C:26]3[C:31]([Cl:32])=[CH:30][N:29]=[CH:28][C:27]=3[Cl:33])=[CH:20][CH:19]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:4]([O:6][CH3:7])=[O:5])=[O:10])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 131723544HCID 131723544, compound

Product 1

HCID 73443602HCID 73443602, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (O) (10 mol %, 58 mg) was added to a mixture of the compound of Example 13, Isomer A (288 mg, 0.493 mmol) and phenyl boronic acid (90 mg, 0.74 mmol) in DME (10 ml) and sodium carbonate (2M, 0.986 mmol, 0.493 ml). The mixture was heated at 80° overnight, dlute with CH2Cl2 (200 ml), washed with diluted HCl and sodium hydrogen carbonate solution, dried (Na2SO4) and evaporated in vacuo. Chromatography (SiO2; CH2Cl2/MeOH, 93:7) gave the title compound as a white solid (133 mg). δH (DMSO-d6), 11.04 (1H, s, CONH), 10.40 (1H, s, CONH), 8.79 (2H, s, Cl2PyH), 8.48 (1H, dd, J 4.9, 1.9 Hz, PyH), 7.85 (1H, dd, J 7.5, 1.9 Hz, PyH), 7.66 (2H, d, J 8.7 Hz, ArH), 7.51 (1H, dd, J 7.5, 4.9 Hz, PyH), 7.39-7.35 (3H, m, ArH), 7.23 (2H, d, J 8.7 Hz, ArH), 7.07 (2H, m, ArH) and 3.45 (3H, s, CO2Me); m/z (ESI, 60V) 581 (MH+).

Workup

  1. temperatureThe mixture was heated at 80° overnight
  2. washwashed with diluted HCl and sodium hydrogen carbonate solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c85a4aa060d42b0a2fff181d5b7d1fa
Source dataset
uspto-grants-2002_10
Patent number
US06465471B1

Reaction notes

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