Methanol → HCID 68515064, compound

HRID 2241402Notes

Reaction equation

HRID 2241402 reaction equation
[CH3:1][O:2][C:3]1[CH:44]=[CH:43][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10](I)=[N:9]2)=[CH:5][CH:4]=1.CN([CH:48]=[O:49])C.C(N(CC)CC)C.[CH3:57][OH:58]>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[F:41][C:19]1[CH:20]=[C:21]([NH:24][C:25]([C:27]2[C:28](=[O:40])[N:29]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[N:30]=[CH:31][CH:32]=2)=[O:26])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:43]=[CH:44][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:9]=[C:10]([C:57]([O:49][CH3:48])=[O:58])[C:11]=12

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 68513145HCID 68513145, compound

Product 1

HCID 68515064HCID 68515064, compound

Reagents, catalysts & solvents 1

HCID 178477754HCID 178477754, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

To a suspension of N-(4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (1.0 g, 1.42 mmol; prepared as in Example 7, Step B) in 1:2 DMF:MeOH (60 mL) was added triethylamine (0.434 ml, 3.11 mmol) and 1,1-bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.116 g, 0.142 mmol). The mixture was purged with N2(g) and CO(g) and then held under balloon pressure CO(g). The mixture was heated at 70° C. and stirred overnight (18 hours). The heat was removed and the excess solvent was evaporated. Diethyl ether (100 mL) was added and the resulting solid removed by filtration to afford the desired product as white solid. Yield (735 mg, 81%). LRMS (APCI pos) m/e 639.1 (M+H).

Workup

  1. customThe mixture was purged with N2(g) and CO(g)
  2. customThe heat was removed
  3. customthe excess solvent was evaporated
  4. additionDiethyl ether (100 mL) was added
  5. customthe resulting solid removed by filtration

Sources & evidence

ORD record
ord-f69d873e752a483d84de4aa0eac2d24b
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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