Diisopropylethylamine → HCID 90011193, compound

HRID 1481482Notes

Reaction equation

HRID 1481482 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]3[C:21]([CH3:23])([CH3:22])[C:20](=[O:24])[NH:19][N:18]=3)=[N:9]2)=[N:6][CH:7]=1.[CH3:25]CN(C(C)C)C(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:15])([F:16])[F:14])=[CH:11][C:10]([C:17]3[C:21]([CH3:22])([CH3:23])[C:20](=[O:24])[N:19]([CH3:25])[N:18]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 90011292HCID 90011292, compound

Product 1

HCID 90011193HCID 90011193, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Step-3: 1′-(5-Bromopyridin-2-yl)-4,4-dimethyl-5′-(trifluoromethyl)-1H, 1′H-[3,3′-bipyrazol]-5(4H)-one: To a stirred and (0° C.) cooled solution of step-2 intermediate (2.0 g, 4.76 mmol) and DIPEA (1.66 mL, 9.52 mmol) in DCM (20 mL) was added a solution of triphosgene (560 mg, 1.90 mmol) in DCM (5 mL) over a period of 10 min. The reaction mixture was warmed to room temperature and then stirred overnight. Reaction was cooled down to 0° C. and then quenched with ice water (5 mL). Water (25 mL) was added to the reaction followed by DCM (50 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 1.50 g (78%) of the title compound as semisolid. 1HNMR (400 MHz, CDCl3) δ 8.85 (s, 1H, D2O exchangeable), 8.59 (d, J=2.0 Hz, 1H), 8.02 (dd, J=2.0 & 8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.31 (s, 1H), 1.60 (s, 6H); ESI-MS (m/z) 402, 404 [(MH)+, Br79,81].

Workup

  1. customReaction
  2. temperaturewas cooled down to 0° C.
  3. customquenched with ice water (5 mL)
  4. additionWater (25 mL) was added to the reaction
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  7. washThe combined organic layers were washed with brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-76baf465e15e4af3b06b6878c1beb0b4
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

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