1,2-Dimethoxyethane → HCID 67116900, compound

HRID 244050Notes

Reaction equation

HRID 244050 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=4I)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1.CO[CH2:29][CH2:30]OC>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:13][CH:12]3[CH2:14][N:15]([C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=4[C:30]4[CH:29]=[CH:6][CH:7]=[CH:2][N:3]=4)=[O:18])[CH2:16][CH:11]3[CH2:10]2)[N:3]=1

Participants

3

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 67116320HCID 67116320, compound

Product 1

HCID 67116900HCID 67116900, compound

Conditions

Temperature
160 °C

Procedure

(5-(4,6-Dimethylpyrimidin-2-yl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(3-fluoro-2-iodophenyl)methanone (51 mg, 0.11 mmol) and 2-tributylstannane pyridine (57 mg, 0.13 mmol) were combined and dissolved in degassed DME then purged with bubbling N2 for 5 minutes. The reaction was treated with Pd(PPh3)4 and then purged with bubbling for 5 minutes in a sealed vessel and then heated to 160° C. in microwave for 90 min. Reaction was filtered through celite, concentrated and purified on 16 g SiO2 with 0-3.5% NH3 MeOH/CH2Cl2. MS (ESI) mass calcd. for C24H24FN5O, 417.49; m/z found, 418.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.71-7.64 (m, 1H), 7.57-7.52 (m, 1H), 7.46 (dddd, J=8.2, 5.6, 2.8, 1.2 Hz, 1H), 7.37 (td, J=7.9, 5.5 Hz, 1H), 7.30-7.24 (m, 2H), 7.20 (ddd, J=9.0, 2.5, 1.5 Hz, 1H), 7.11 (tdd, J=8.4, 2.6, 1.0 Hz, 1H), 6.31 (s, 1H), 3.97 (dd, J=12.7, 7.8 Hz, 1H), 3.89 (dd, J=11.5, 7.7 Hz, 1H), 3.82-3.70 (m, 2H), 3.70-3.60 (m, 2H), 3.50 (dd, J=11.5, 4.6 Hz, 1H), 3.40 (dd, J=10.9, 5.4 Hz, 1H), 3.07 (d, J=7.2 Hz, 1H), 3.03-2.94 (m, 1H), 2.30 (s, 6H).

Workup

  1. customthen purged with bubbling N2 for 5 minutes
  2. additionThe reaction was treated with Pd(PPh3)4
  3. custompurged
  4. customwith bubbling for 5 minutes in a sealed vessel
  5. customReaction
  6. filtrationwas filtered through celite,
  7. concentrationconcentrated
  8. custompurified on 16 g SiO2 with 0-3.5% NH3 MeOH/CH2Cl2

Sources & evidence

ORD record
ord-21dfe32934ab4952a98c761c65d024e3
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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