Sodium Carbonate → 3-(5-(ethoxycarbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzoic acid

HRID 882130Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].Cl[C:14]1[C:15]2[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][NH:20][C:16]=2[N:17]=[CH:18][N:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd]>[CH2:26]([O:25][C:23]([C:22]1[C:15]2[C:14]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:1]([OH:3])=[O:2])=[N:19][CH:18]=[N:17][C:16]=2[NH:20][CH:21]=1)=[O:24])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 3-carboxyphenyboronic acid (215 mg, 1.30 mmol) and ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (195 mg, 0.864 mmol) in 2 M aqueous sodium carbonate (2.0 mL, 2.1 mmol) and dioxane (8.0 mL) was added SiliaCat® heterogeneous catalysts DPP-Pd (loading=0.28 mmol/g, 617 mg, 0.173 mmol). The reaction mixture was purged with argon and heated to 100° C. overnight. The reaction mixture was filtered and rinsed with ethyl acetate and methanol. The reaction solution was concentrated under reduced pressure to give 3-(5-(ethoxycarbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzoic acid which was used for next step without further purification. LRMS (ESI) calc'd for C16H14N3O4 [M+H]+: 312, found 312.

Workup

additionwas added SiliaCat® heterogeneous catalysts
customThe reaction mixture was purged with argon
filtrationThe reaction mixture was filtered
washrinsed with ethyl acetate and methanol
concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-4150bdba04a048108b57618e3a1fd6f3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993756B2

Reaction notes

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