1,2-Dimethoxyethane → HCID 86696335, compound

HRID 870641Notes

Reaction equation

HRID 870641 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:30]=[CH:29][C:28]([CH:31]3[CH2:35][CH2:34][CH2:33][N:32]3[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:27][CH:26]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COCCOC>O>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:25]3[CH:26]=[CH:27][C:28]([CH:31]4[CH2:35][CH2:34][CH2:33][N:32]4[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:29][CH:30]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 56973658HCID 56973658, compoundHCID 86696336HCID 86696336, compound

Product 1

HCID 86696335HCID 86696335, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 150 mg (0.530 mmol) of the 3-bromo-N-pentylimidazo[1,2-b]pyridazin-6-amine was added the tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine-1-carboxylate (237 mg, 0.636 mmol), K3PO4 (225 mg, 1.060 mmol), PdCl2(PPh3)3 (37 mg, 0.053 mmol), 3 mL of DME and 1 mL of water. This mixture was microwaved for 0.5 hr at 140° C. After cooling it was diluted with 25 mL of EtOAC, and washed with about 20 mL of brine. The organic layer was dried over MgSO4, and concentrated. The crude mixture was purified on a 12 g silica gel column (ISCO), eluting with 15-100% EtOAc/Hex to give 159 mg (67%) of the desired product.

Workup

  1. customThis mixture was microwaved for 0.5 hr at 140° C
  2. temperatureAfter cooling it
  3. additionwas diluted with 25 mL of EtOAC
  4. washwashed with about 20 mL of brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude mixture was purified on a 12 g silica gel column (ISCO)
  8. washeluting with 15-100% EtOAc/Hex

Sources & evidence

ORD record
ord-70ae4c463b3f4faca7cf58e4d2878b82
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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