Sodium Carbonate → HCID 117857099, compound

HRID 1750332Notes

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][CH:21]=[C:20](B(O)O)[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:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=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-3-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 16 h. The reaction mixture was cooled down and partitioned between saturated sodium bicarbonate (35 mL) and DCM (35 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 (280 mg, 90%). LCMS RT=0.647 min, M+H+=309.1

Workup

customwas degassed
temperatureThe reaction mixture was cooled down
custompartitioned between saturated sodium bicarbonate (35 mL) and DCM (35 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-41cc23c6c5504f0e8af36e638751fb7c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156853B2

Reaction notes

Loading…