Bicarbonate Ion → 4-Ethoxy-3-(1-methyl-6-oxopyridin-3-yl)benzenesulfonamide

HRID 518331Notes

Reaction equation

[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]1=[O:17].Br[C:19]1[CH:20]=[C:21]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:22]=[CH:23][C:24]=1[O:25][CH2:26][CH3:27].C(=O)(O)[O-]>O1CCOCC1.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]>[CH2:26]([O:25][C:24]1[CH:19]=[CH:20][C:21]([S:28]([NH2:31])(=[O:29])=[O:30])=[CH:22][C:23]=1[C:6]1[CH:5]=[CH:4][C:3](=[O:17])[N:2]([CH3:1])[CH:7]=1)[CH3:27]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of the title compound of Example 98, step 1 (40 mg, 0.17 mmol), Pd(dppf)Cl2 (10 mg, 8%) and 3-bromo-4-ethoxybenzene-1-sulfonamide (48 mg, 0.17 mmol) was suspended in 1,4-dioxane (880 μL) and saturated bicarbonate solution (aq) (220 μL). The mixture was heated to 95° C. using microwave irradiation (normal) for 60 min. The crude reaction mixture was filtered through a short plug of celite, the plug was washed with additional 1,4-dioxane (1 ml), and the combined filtrate was purified by prep-HPLC. The fractions were combined and lyophilized to give the title compound (14 mg, 27%) as a white solid. 1HNMR (DMSO, 400 MHz): δ 1.33 (t, J=6.9, 3 H), 3.49 (s, 3H), 4.15 (q, J=6.9, 2H), 6.45 (d, J=9.4 Hz, 1H), 7.20-7.23 (m, 3H), 7.64 (dd, J=2.6, 9.4 Hz, 1H), 7.72-7.74 (m, 2H), 7.89 (d, J=2.6 Hz, 1H). LCMS (M+H)+=309.

Workup

custommicrowave irradiation (normal) for 60 min
customThe crude reaction mixture
filtrationwas filtered through a short plug of celite
washthe plug was washed with additional 1,4-dioxane (1 ml)
customthe combined filtrate was purified by prep-HPLC

Sources & evidence

ORD record: ord-6687920ceed3403aa8feabf61d2ed2c1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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