Water → HCID 57856234, compound

HRID 500745Notes

Reaction equation

HRID 500745 reaction equation
I[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]=2)=[CH:5][N:4]([CH:13]([CH3:15])[CH3:14])[N:3]=1.[Cl:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[C:23](B3OC(C)(C)C(C)(C)O3)[CH:24]=2)[NH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].Cl[Pd]Cl>[Cl:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[C:23]([C:2]3[C:6]([C:7]4[CH:12]=[CH:11][N:10]=[CH:9][N:8]=4)=[CH:5][N:4]([CH:13]([CH3:15])[CH3:14])[N:3]=3)[CH:24]=2)[NH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 57856322HCID 57856322, compoundHCID 59424413HCID 59424413, compound

Product 1

HCID 57856234HCID 57856234, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(3-Iodo-1-isopropyl-1H-pyrazol-4-yl)-pyrimidine (0.05 g, 0.2 mmol), 3-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.089 g, 0.318 mmol) and 2 M aq Na2CO3 (0.067 g, 0.636 mmol, 0.318 mL 3.0 Eq) in DMF (4 mL) was bubbled with Nitrogen for 15 min and DPPF PdCl2 (0.0140 g, 0.019 mmol, 0.06 Eq) was added and then heated in biotage microwave initiator for 2.0 hour at 100° C. and under a high absorption. The resultant black reaction was cooled to room temperature. The reaction was poured into H2O (100 mL) and extracted (3×50 mL EtOAC). The combined organics were dried over Na2SO4 and concentrated in vacuo to a black oil which was purified by Biotage column (Si 25+M) packed with hexanes and eluted with (5% MeOH/EtOAc)/Hexanes (0-50%:700 mL, 50-100%:700 mL, 100%; 700 mL, 27 mL fractions) to yield the product F-1 as an off-white solid (0.025, 50%).

Workup

  1. customwas bubbled with Nitrogen for 15 min
  2. customThe resultant black reaction
  3. temperaturewas cooled to room temperature
  4. extractionextracted (3×50 mL EtOAC)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo to a black oil which
  7. customwas purified by Biotage column (Si 25+M)
  8. washeluted with (5% MeOH/EtOAc)/Hexanes (0-50%:700 mL, 50-100%:700 mL, 100%; 700 mL, 27 mL fractions)
  9. customto yield the product F-1 as an off-white solid (0.025, 50%)

Sources & evidence

ORD record
ord-fc1ae9861c6e4e9c9fe5e79d9371312f
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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