Sodium Bicarbonate → HCID 58504704, compound

HRID 2367559Notes

Reaction equation

HRID 2367559 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[F:12])#[N:2].Cl[C:14]1[N:19]=[C:18]([NH:20][CH3:21])[N:17]=[C:16]([N:22]2[C@H:27]([CH2:28][CH3:29])[CH2:26][O:25][C@H:24]([C:30]([NH:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:31])[CH2:23]2)[CH:15]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:14]2[N:19]=[C:18]([NH:20][CH3:21])[N:17]=[C:16]([N:22]3[C@H:27]([CH2:28][CH3:29])[CH2:26][O:25][C@H:24]([C:30]([NH:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[O:31])[CH2:23]3)[CH:15]=2)=[CH:5][C:4]=1[F:12])#[N:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 58504661HCID 58504661, compound

Product 1

HCID 58504704HCID 58504704, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Cyano-3-fluorophenyl)boronic acid (0.261 g, 1.582 mmol) was added to a 20 mL microwave vessel followed by the addition of Pd(PPh3)4 (0.046 g, 0.040 mmol) and (2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-N-cyclohexyl-5-ethyl-2-morpholinecarboxamide (0.302 g, 0.791 mmol) dissolved in 1,4-dioxane (5 mL). Saturated aqueous NaHCO3 (2.5 mL) was added and the reaction was irradiated at 130° C. for 30 minutes. SiliaBond® Thiol (3.04 g, 3.96 mmol) was added to the reaction and it was stirred at room temperature for 2 hours and then filtered. The filtrate was then diluted with H2O and extracted with EtOAc (2×). The organics were dried and concentrated to afford the crude title compound (0.387 g) as a dark brown oil. LC-MS (ES) m/z=467 [M+H]+.

Workup

  1. customthe reaction was irradiated at 130° C. for 30 minutes
  2. filtrationfiltered
  3. additionThe filtrate was then diluted with H2O
  4. extractionextracted with EtOAc (2×)
  5. customThe organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc3bbcefdaec45d5b5a350d5d742242c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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