2-Bromo-5-fluoropyridine → HCID 90386053, compound

HRID 2281230Notes

Reaction equation

HRID 2281230 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:18][C:19](=[O:29])[O:20][C@H:21]4[CH:26]5[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]5)[CH2:22]4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)O1.Br[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][N:33]=1>>[F:38][C:35]1[CH:36]=[CH:37][C:32]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:18][C:19](=[O:29])[O:20][C@H:21]4[CH:26]5[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]5)[CH2:22]4)[CH2:16][CH2:17]3)=[CH:11][CH:10]=2)=[N:33][CH:34]=1

Participants

3

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 131733412HCID 131733412, compound

Product 1

HCID 90386053HCID 90386053, compoundYield 34%

Procedure

Using general procedure E, (S)-quinuclidin-3-yl (1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)phenyl)cyclopropyl)carbamate, 2-bromo-5-fluoropyridine and [PdCl2(pddf)]CH2Cl2 gave the title compound as a white solid (34%). 1H NMR (500 MHz, CDCl3) δ 8.51-8.52 (d, J=3.5 Hz, 1H), 7.87-7.85 (d, J=10.5 Hz, 2H), 7.69-7.67 (m, 1H), 7.47-7.42 (m, 1H), 7.32-7.27 (m, 2H), 5.79-5.66 (d, 1H), 4.73-4.71 (t, J=5.0 Hz, 1H), 3.22-3.19 (m, 1H), 2.87-2.61 (m, 5H), 2.01-1.22 (m, 9H) ppm. 13C NMR (125 MHz, CDCl3) δ 160.8, 157.4, 156.1, 153.5, 144.4, 137.8, 136.3, 126.7, 125.7, 124.9, 123.6, 121.1, 71.6, 55.7, 47.4, 46.5, 35.3, 29.7, 25.4, 24.8, 19.4, 18.2 ppm. Purity: >99% LCMS (214 nm & 254 nm); retention time 1.41 min; (M+1) 382.2.

Sources & evidence

ORD record
ord-02fc623547724b25a341da801173794a
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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