Potassium Carbonate → methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate

HRID 2190168Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:15]([C:16]([NH:18][CH3:19])=[O:17])=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[O:13][C:5]2=[N:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39]>CC(N(C)C)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:15]([C:16](=[O:17])[NH:18][CH3:19])=[C:14]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[O:13][C:5]2=[N:6][C:7]=1[N:8]([CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[S:9]([CH3:12])(=[O:10])=[O:11]

Participants

Conditions

Temperature: 150 °C

Procedure

5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (100 mg, 0.206 mmol) was dissolved in dimethylacetamide (10 mL) and K2CO3 (39.9 mg, 0.288 mmol) was added then followed by methyl 5-bromopentanoate (0.059 mL, 0.412 mmol). The mixture was heated at 150° C. in the microwave for 20 min. Conversion approx 75% by LCMS, after which addition of additional methyl 5-bromopentanoate (3 eqs) and K2CO3 (2 eqs) did not result in additional conversion. Filtration and purification by HPLC (TFA/CH3CN/H2O) afforded 57 mg (0.095 mmol, 46%) methyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)pentanoate MS-ES [M+H]+=599.8, LC RT=1.61 min, Method A.

Workup

customdid not result in additional conversion
filtrationFiltration and purification by HPLC (TFA/CH3CN/H2O)

Sources & evidence

ORD record: ord-dd96763b697347cd9bb4553307dbdfcb
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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