Methanol → HCID 118093679, compound

HRID 629298Notes

Reaction equation

HRID 629298 reaction equation
[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH:11][CH3:12])[C:8]([N+:13]([O-])=O)=[CH:7][C:6]=1[C:16]1[C:17]2[CH:26]=[CH:25][N:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:18]=2[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=1.CO.[Cl-].[NH4+]>C(OCC)(=O)C.ClCCl.[Zn]>[NH2:13][C:8]1[C:9]([NH:11][CH3:12])=[CH:10][C:5]([O:4][C:3]2[CH:37]=[CH:38][C:39]([F:41])=[CH:40][C:2]=2[F:1])=[C:6]([C:16]2[C:17]3[CH:26]=[CH:25][N:24]([S:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)(=[O:29])=[O:28])[C:18]=3[C:19](=[O:23])[N:20]([CH3:22])[CH:21]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 118093663HCID 118093663, compound

Product 1

HCID 118093679HCID 118093679, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[2-(2,4-difluorophenoxy)-4-(methylamino)-5-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.150 g, 0.258 mmol) in ethyl acetate (1.0 mL) was treated with methanol (1.0 mL) and saturated aqueous ammonium chloride solution (0.225 mL, 3.36 mmol) and cooled to 0° C. The reaction mixture was treated with zinc (0.135 g, 2.07 mmol) in two portions over 5 minutes. The reaction mixture was heated at 55° C. for 10 min, diluted with dichloromethane, filtered over Celite, and washed with dichloromethane. The filtrate was concentrated to residue. The residue was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (20 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (0.141 g, 99%), which was used without further purification. LCMS calculated for C28H25F2N4O4S (M+H)+: m/z=551.2. found: 550.9.

Workup

  1. temperatureThe reaction mixture was heated at 55° C. for 10 min
  2. filtrationfiltered over Celite
  3. washwashed with dichloromethane
  4. concentrationThe filtrate was concentrated to residue
  5. dissolutionThe residue was dissolved in dichloromethane (30 mL)
  6. washwashed with saturated sodium bicarbonate solution (20 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9e7196e2ad0b4069a7773fb27be28e78
Source dataset
uspto-grants-2016_04
Patent number
US09315501B2

Reaction notes

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