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1-Cyclopropylethanamine → 1-[(1-Cyclopropylethyl)amino]-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971022
Notes
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Reaction equation

HRID 1971022 reaction equation
Cl[C:2]1[C:14]2[C:13]3[CH:12]=[C:11]([F:15])[CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:16]#[N:17])=[CH:4][N:3]=1.[CH:18]1([CH:21]([NH2:23])[CH3:22])[CH2:20][CH2:19]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:18]1([CH:21]([NH:23][C:2]2[C:14]3[C:13]4[CH:12]=[C:11]([F:15])[CH:10]=[CH:9][C:8]=4[NH:7][C:6]=3[C:5]([C:16]#[N:17])=[CH:4][N:3]=2)[CH3:22])[CH2:20][CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5192391-CyclopropylethanamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 591984921-chloro-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 595431621-[(1-Cyclopropylethyl)amino]-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst

Conditions

Temperature
85 °C

Procedure

1-Chloro-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile (400 mg, 1.63 mmol), 1-cyclopropylethanamine (594 mg, 4.89 mmol), Pd2(dba)3 (74.6 mg, 0.081 mmol), BINAP (152 mg, 0.24 mmol), and sodium tert-butoxide (782 mg, 8.14 mmol) were placed in a sealed tube. The mixture was evacuated and backfilled with argon three times. Fully degassed DME (8.1 ml) was added. The tube was sealed and the reaction was heated to 85° C. and stirred for 20 hrs. The reaction was cooled to ambient temperature, concentrated in vacuo, and directly purified via flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C17H16FN4) [M+H]+, 295.1. found 295.0.

Workup

  1. customThe mixture was evacuated
  2. additionFully degassed DME (8.1 ml) was added
  3. customThe tube was sealed
  4. temperatureThe reaction was cooled to ambient temperature
  5. concentrationconcentrated in vacuo
  6. customdirectly purified via flash chromatography

Sources & evidence

ORD record
ord-bd8a8a6b38d14496af9496567f395c29
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431569B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes