Sodium Bicarbonate → HCID 58504512, compound

HRID 2367563Notes

Reaction equation

HRID 2367563 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][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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 58504678HCID 58504678, compound

Product 1

HCID 58504512HCID 58504512, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4-Cyano-3-fluorophenyl)boronic acid (0.266 g, 1.61 mmol) was added to a 20 mL microwave vessel followed by the addition of Pd(PPh3)4 (0.047 g, 0.040 mmol) and (2S,5R)-4-[6-chloro-2-(methylamino)-4-pyrimidinyl]-5-ethyl-N-(phenylmethyl)-2-morpholinecarboxamide (0.314 g, 0.805 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 (3.10 g, 4.03 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 title compound (0.365 g) as a dark brown oil. LC-MS (ES) m/z=475 [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-b88f7702398d401a9744ef48577bcbe2
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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