2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate → HCID 58044000, compound

HRID 1919086Notes

Reaction equation

HRID 1919086 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][N:16]([CH2:21][CH3:22])[CH2:15][CH2:14][C:13]=3[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C([O:26][CH2:27][C:28]1[C:33]([N:34]2[CH2:45][CH2:44][N:43]3[C:36](=[CH:37][C:38]4[CH2:39][C:40]([CH3:47])([CH3:46])[CH2:41][C:42]=43)[C:35]2=[O:48])=[CH:32][C:31]([F:49])=[CH:30][C:29]=1B1OC(C)(C)C(C)(C)O1)(=O)C>C([O-])([O-])=O.[Na+].[Na+].COCCOC.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>[CH2:21]([N:16]1[CH2:15][CH2:14][C:13]2[N:12]=[C:11]([NH:10][C:4]3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([C:29]4[C:28]([CH2:27][OH:26])=[C:33]([N:34]5[CH2:45][CH2:44][N:43]6[C:36](=[CH:37][C:38]7[CH2:39][C:40]([CH3:46])([CH3:47])[CH2:41][C:42]=76)[C:35]5=[O:48])[CH:32]=[C:31]([F:49])[CH:30]=4)[CH:3]=3)[CH:20]=[CH:19][C:18]=2[CH2:17]1)[CH3:22]

Participants

6

Reactant 2

HCID 670162322-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetateHCID 67016494HCID 67016494, compound

Product 1

HCID 58044000HCID 58044000, compoundYield 7.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

In a 48-mL sealed tube equipped with a magnetic stirring bar were placed 5-bromo-1-methyl-3-(6-ethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-ylamino)pyridin-2(1H)-one (143 mg, 0.4 mmol), 10-[2-(acetoxymethyl)-3-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-5-fluorophenyl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]-dodeca-2(6),7-dien-9-one 230a (496 mg, 1.0 mmol), Pd(PPh3)4 (23 mg, 0.020 mmol) in 2 N Na2CO3 (4 mL) and DME (4 mL). After the reaction mixture was stirred at 100° C. for 1 h, it was purified by flash chromatography (dichloromethane:methanol, 3:1) to give 7% (18 mg) of 284 MS (ESI+) m/z 611.5 (M+H).

Workup

  1. customIn a 48-mL sealed tube
  2. customequipped with a magnetic stirring bar
  3. customit was purified by flash chromatography (dichloromethane:methanol, 3:1)

Sources & evidence

ORD record
ord-e9f207d0a4ae4dfa9fe7944740ba63c3
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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