Methanol → HCID 66767226, compound

HRID 1661985Notes

Reaction equation

HRID 1661985 reaction equation
[CH:1]1([C:4]2[C:5]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][C:21]=3[F:29])=[CH:6][C:7]3[C:11]([CH:12]=2)=[N:10][N:9]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=3)[CH2:3][CH2:2]1.CO.CN(C)N>CCOC(C)=O.C(Cl)Cl>[CH:1]1([C:4]2[C:5]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:21]=3[F:29])=[CH:6][C:7]3[C:11]([CH:12]=2)=[N:10][N:9]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=3)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887Methanol2×HCID 59761,1-DimethylhydrazineHCID 66766897HCID 66766897, compound

Product 1

HCID 66767226HCID 66767226, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

To a 25 mL glass vial is added 6-cyclopropyl-5-(2-fluoro-4-nitrophenoxy)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (395 mg, 994 μmol) and MeOH (20 mL, 494 mmol). To the suspension is added N,N-dimethylhydrazine (756 μL, 9.94 mmol) and FeCl3 (163 mg, 994 μmol). The vial is capped, and heated to 60° C. and stirred for 2 hours and then stirred at 50° C. overnight. The mixture is filtered over a Buchner funnel and the solid washed with MeOH (100 mL). The filtrate is collected and concentrated to give a brown/orange solid. The residue is purified on a silica gel column eluting with DCM (A) and a 10% MeOH in a DCM solution (B), gradient from 100% (A) to 85%(A): 15%(B) over 50 min to give a yellow solid as the title compound (358 mg, 98% yield). MS (m/z): 368 (M+H).

Workup

  1. customThe vial is capped
  2. stirringstirred at 50° C. overnight
  3. filtrationThe mixture is filtered over a Buchner funnel
  4. washthe solid washed with MeOH (100 mL)
  5. customThe filtrate is collected
  6. concentrationconcentrated
  7. customto give a brown/orange solid
  8. customThe residue is purified on a silica gel column
  9. washeluting with DCM (A)

Sources & evidence

ORD record
ord-011d9683af8d478dbdf1ce3ed9c242fc
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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