Butanoic acid, 2-bromo-, ethyl ester → Methyl 4-(4-(thiophene-2-sulfonamido)naphthalen-1-yloxy)butanoate

HRID 1258395Notes

Reaction equation

HRID 1258395 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:20]CC(OC(C)(C)C)=O)=[CH:12][CH:11]=1)(=[O:8])=[O:7].Br[CH:30]([CH2:36][CH3:37])[C:31]([O:33][CH2:34]C)=[O:32]>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([O:20][CH2:37][CH2:36][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:12][CH:11]=1)(=[O:7])=[O:8]

Participants

3

Reactant 2

HCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 46908189Tert-butyl 2-(4-(thiophene-2-sulfonamido)naphthalen-1-yloxy)acetate

Product 1

HCID 46908190Methyl 4-(4-(thiophene-2-sulfonamido)naphthalen-1-yloxy)butanoateYield 51.3%

Procedure

15b was synthesized according to the procedure for 15a except 15 eq. of ethyl bromobutanoate was used and reaction was carried out at 90° C. for 30 min×2. After flash chromatography, 43 mg product was obtained in the yield of 51.3%. 1H NMR (400 MHz, CDCl3) δ 7.84-7.79 (m, 1H), 7.77 (m, 1H), 7.62 (dd, J=5.0, 1.3 Hz, 1H), 7.58 (dd, J=3.8, 1.3 Hz, 1H), 7.44-7.36 (m, 2H), 7.14 (d, J=8.4 Hz, 0H), 7.00 (dd, J=5.0, 3.9 Hz, 1H), 6.44 (d, J=8.4 Hz, 1H), 4.15 (q, J=7.1 Hz, 1H), 3.31 (t, J=6.7 Hz, 1H), 2.52 (t, J=6.8 Hz, 1H), 2.11 (p, J=6.7 Hz, 1H), 1.25 (t, J=7.1 Hz, 4H).

Workup

  1. customreaction

Sources & evidence

ORD record
ord-02088bca221945b79c3f3332d5598d1b
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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