Sodium Carbonate → HCID 117857366, compound

HRID 1750334Notes

Reaction equation

I[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH:7]=[N:6][C:5]=2[N:4]([CH3:17])[CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.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.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:17][N:4]1[C:5]2[N:6]=[CH:7][N:8]([CH2:12][C:13]([F:16])([F:15])[F:14])[C:9](=[O:11])[C:10]=2[C:2]([C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)=[CH:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-iodo-7-methyl-3-(2,2,2-trifluoroethyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (358 mg, 1.00 mmol), pyridin-4-ylboronic acid (148 mg, 1.20 mmol), sodium carbonate (319 mg, 3.01 mmol) and PdCl2(dppf)-CH2Cl2 adduct (82 mg, 0.100 mmol) in 1,4-dioxane (8 ml) and water (1.5 ml) was degassed. The resulting mixture was heated at 70° C. for 48 h. The reaction mixture was cooled and partitioned between saturated sodium bicarbonate solution (100 ml) and DCM (100 ml). The organic phase was separated and concentrated in vacuo. The remaining residue was purified by flash chromatography (0-100% ethyl acetate/cyclohexane) to afford the title compound (105 mg, 34%). LCMS RT=0.64 min, M+H+=309.1

Workup

customwas degassed
temperatureThe reaction mixture was cooled
custompartitioned between saturated sodium bicarbonate solution (100 ml) and DCM (100 ml)
customThe organic phase was separated
concentrationconcentrated in vacuo
customThe remaining residue was purified by flash chromatography (0-100% ethyl acetate/cyclohexane)

Sources & evidence

ORD record: ord-6aeedd50ca4943189a1b18b234306825
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156853B2

Reaction notes

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