4-Bromo-3-nitroanisole → HCID 59282885, compound

HRID 1965852Notes

Reaction equation

HRID 1965852 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.CC1(C)C(C)(C)OB([C:21]2[S:22][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:25]=2)O1.Br[C:37]1[CH:38]=[N:39][CH:40]=[C:41]([F:43])[CH:42]=1>>[F:43][C:41]1[CH:42]=[C:37]([C:23]2[S:22][C:21]3[C:2]4[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=4[NH:10][C:25]=3[CH:24]=2)[CH:38]=[N:39][CH:40]=1

Participants

4

Reactant 3

HCID 792884-Bromo-3-nitroanisoleHCID 8202063-Bromo-5-fluoropyridineHCID 230580612,2'-(Thiene-2,5-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Product 1

HCID 59282885HCID 59282885, compoundYield 6.7%

Procedure

Compound 2-(5-fluoropyridin-3-yl)-6-methoxy-4H-thieno[3,2-b]indole (W309) was synthesized using the same procedure for the preparation of W270 from 1-bromo-4-methoxy-2-nitrobenzene (104 mg, 0.45 mmol), 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene (168 mg, 0.5 mmol), and 3-bromo-5-fluoropyridine (105 mg, 0.6 mmol), as a yellow solid (10 mg, total yield 6.7%). 1H NMR (400 MHz, acetone-d6) δ 10.36 (brs, 1 H), 8.76 (s, 1 H), 8.33 (s, 1 H), 7.83 (m, 2 H), 7.77 (m, 1 H), 7.62-7.60 (m, 1 H), 7.02 (s, 1 H), 6.80 (d, J=8.8 Hz, 1 H), 3.86 (s, 3 H); MS (ESI) m/z 299 (M+H+).

Sources & evidence

ORD record
ord-6457d6f35d4b42f182e30a656d5d7574
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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