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Potassium Carbonate → HCID 23653815, compound

HRID 597923
Notes
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Reaction equation

HRID 597923 reaction equation
BrC1C(OC)=NC2CCN(C(=O)C(F)(F)F)CC(C)C=2C=1.[Sn](C=C)(CCCC)(CCCC)CCCC.[CH3:37][O:38][C:39]1[C:40]([CH:57]=[CH2:58])=[CH:41][C:42]2[CH:48]([CH3:49])[CH2:47][N:46](C(=O)C(F)(F)F)[CH2:45][CH2:44][C:43]=2[N:56]=1.C([O-])([O-])=O.[K+].[K+]>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.O.CO.C1(C)C=CC=CC=1>[CH3:37][O:38][C:39]1[C:40]([CH:57]=[CH2:58])=[CH:41][C:42]2[CH:48]([CH3:49])[CH2:47][NH:46][CH2:45][CH2:44][C:43]=2[N:56]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 81998TributylvinyltinHCID 23654109HCID 23654109, compoundHCID 23654281HCID 23654281, compound

Product 1

HCID 23653815HCID 23653815, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 887MethanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-bromo-2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro -5H-pyrido[2,3-d]azepine (220 mg, 599 μmol), Bu3SnCH═CH2 (523 μl, 1.79 mmol), Pd(PPh3)4 (50 mg), and toluene (10 ml) was heated in a sealed tube at 110° C. for 16 h. The solvent was evaporated and the resulting residue was purified by column chromatography to render 165 mg (88%) of 2-methoxy-5-methyl-7-(trifluoroacetyl)-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. A mixture of 2-methoxy-5-methyl-7-(trifluoroacetyl)-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (32 mg, 102 μmol), K2CO3 (40 mg), MeOH (5 ml) and H2O (1 ml) was heated to reflux for 10 min. The reaction mixture was concentrated in vacuo and the resulting residue was purified by column chromatography to yield 17.0 mg (77%) of 2-methoxy-5-methyl-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ 7.58 (s, 1H), 6.92 (dd, 1H), 5.86 (d, 1H), 5.40 (d, 1H), 4.02 (s, 3H), 3.60-3.40 (m, 4H), 3.31 (m, 1H), 3.18 (dd, 1H), 3.00 (m, 1H), 1.52 (d, 3H) ppm.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue was purified by column chromatography
  3. temperaturewas heated
  4. temperatureto reflux for 10 min
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c04d402e6e44850ac4d80f992ca9724
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897595B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes