Acetic Acid → HCID 66604445, compound

HRID 2410893Notes

Reaction equation

HRID 2410893 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:12]=2)[CH:3]=1.CC(O)=[O:27]>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[C:3]2[C:12]3[C:11](=[CH:16][CH:15]=[C:14]([C:17]([N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)=[O:18])[CH:13]=3)[NH:10][C:4]=2[C:5]([C:6]([NH2:7])=[O:27])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66604568HCID 66604568, compound

Product 1

HCID 66604445HCID 66604445, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
160 °C

Procedure

4-Fluoro-2-(4-(morpholine-4-carbonyl)phenylamino)benzonitrile (100 mg, 0.246 mmol) was mixed with Pd(OAc)2 (138 mg, 0.615 mmol) in AcOH (7 mL) in a sealed microwave tube. The mixture was heated in microwave at 160° C. for 90 mins. The mixture was filtered and washed with 5 ml AcOH. The filtrate was concentrated and purified using preparative HPLC to give 4-fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/z 342.13 (M+H). 1H NMR (DMSO-d6) δ ppm 11.87 (s, 1H), 8.19 (s, 1H), 8.11 (s, 1H), 8.03 (dd, 1H, J=8.3, 5.0), 7.83(d, 1H, J=8.6), 7.53 (m, 2H), 7.08(m, 1H), 3.64-3.57 (bm, 8H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with 5 ml AcOH
  3. concentrationThe filtrate was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-b319ea2bd9d4442b9c083b80c4fdb62a
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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