2-Bromo-5-fluoropyridine → 3-[4-(5-Fluoropyridin-2-yl)phenyl]propionaldehyde

HRID 1927662Notes

Reaction equation

CC(C1NC(=O)C(CCSC)NC(=O)C(NC(C(NC(C(NC(C(NC(C(N)CC(O)=O)=O)C(O)C)=O)CCSC)=O)CCCNC(N)=N)=O)CSSCC(C(NC(C(NC(C(NC(C(O)=O)C(C)C)=O)CCC(O)=O)=O)CC2C3C(=CC=CC=3)NC=2)=O)NC(=O)C2N(CCC2)C(=O)C(CCCNC(N)=N)N[C:21](=[O:22])[CH:20]([CH2:127][C:128]2[CH:133]=[CH:132][C:131](O)=[CH:130][CH:129]=2)NC(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC1=O)C.IC1C=CC=CC=1C(OC(C)(C)C)=O.Br[C:160]1[CH:165]=[CH:164][C:163]([F:166])=[CH:162][N:161]=1>>[F:166][C:163]1[CH:164]=[CH:165][C:160]([C:131]2[CH:130]=[CH:129][C:128]([CH2:127][CH2:20][CH:21]=[O:22])=[CH:133][CH:132]=2)=[N:161][CH:162]=1

Participants

Reactant 3

HCID 27831712-Bromo-5-fluoropyridine

HCID 11438134Tert-butyl 2-iodobenzoate

HCID 16167454Melanin-concentrating hormone

Product 1

HCID 594435643-[4-(5-Fluoropyridin-2-yl)phenyl]propionaldehyde

Procedure

The title compound was prepared following the procedure described for intermediate 1 substituting tert-butyl 2-iodobenzoate with 2-bromo-5-fluropyridine. 1H NMR (500 MHz, CDCl3) δ 9.83 (s, 1H), 8.52 (d, J=2.9 Hz, 1H), 7.86 (d, J=8.2 Hz, 2H), 7.67-7.70 (m, 1H), 7.42-7.46 (m, 1H), 7.29 (d, J=8.2 Hz, 2H), 3.0 (t, J=7.6 Hz, 2H), 2.82 (t, J=7.3 Hz, 2H).

Sources & evidence

ORD record: ord-5f9a32c4441643d19f1644471888256b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183275B2

Reaction notes

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